In the title compounds, the thiosemicarbazone group adopts an extended conformation, and there is a short N—H
N contact present forming an
S(5) ring motif. In the crystals of both compounds, molecules are linked by pairs of N—H
S hydrogen bonds, forming dimers with
(8) ring motifs.
Supporting information
CCDC references: 1519492; 1519491
Key indicators
Structure: I
- Single-crystal X-ray study
- T = 293 K
- Mean
![[sigma]](https://journals.iucr.org/logos/entities/sigma_rmgif.gif)
(C-C) = 0.003 Å
- R factor = 0.038
- wR factor = 0.109
- Data-to-parameter ratio = 16.5
Structure: II
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.002 Å
- R factor = 0.034
- wR factor = 0.099
- Data-to-parameter ratio = 15.7
checkCIF/PLATON results
No syntax errors found
Datablock: I
Alert level B
PLAT414_ALERT_2_B Short Intra D-H..H-X H2B .. H10B .. 1.86 Ang.
Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for S1A -- C11A .. 5.3 s.u.
PLAT242_ALERT_2_C Low 'MainMol' Ueq as Compared to Neighbors of C2A Check
PLAT242_ALERT_2_C Low 'MainMol' Ueq as Compared to Neighbors of C2B Check
PLAT420_ALERT_2_C D-H Without Acceptor N3A -- H3A2 ... Please Check
Alert level G
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms .............. 6 Report
PLAT154_ALERT_1_G The s.u.'s on the Cell Angles are Equal ..(Note) 0.002 Degree
PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K) 293 Check
PLAT200_ALERT_1_G Reported _diffrn_ambient_temperature ..... (K) 293 Check
PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels .......... 10 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 6 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density 3 Note
0 ALERT level A = Most likely a serious problem - resolve or explain
1 ALERT level B = A potentially serious problem, consider carefully
4 ALERT level C = Check. Ensure it is not caused by an omission or oversight
7 ALERT level G = General information/check it is not something unexpected
3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
6 ALERT type 2 Indicator that the structure model may be wrong or deficient
0 ALERT type 3 Indicator that the structure quality may be low
2 ALERT type 4 Improvement, methodology, query or suggestion
1 ALERT type 5 Informative message, check
Datablock: II
Alert level B
PLAT230_ALERT_2_B Hirshfeld Test Diff for S1 -- C16 .. 8.3 s.u.
Alert level C
PLAT414_ALERT_2_C Short Intra D-H..H-X H2A .. H15A .. 1.96 Ang.
PLAT420_ALERT_2_C D-H Without Acceptor N3 -- H3B ... Please Check
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L= 0.600 4 Report
Alert level G
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms .............. 3 Report
PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K) 293 Check
PLAT200_ALERT_1_G Reported _diffrn_ambient_temperature ..... (K) 293 Check
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 14 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density 13 Note
0 ALERT level A = Most likely a serious problem - resolve or explain
1 ALERT level B = A potentially serious problem, consider carefully
3 ALERT level C = Check. Ensure it is not caused by an omission or oversight
5 ALERT level G = General information/check it is not something unexpected
2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
4 ALERT type 2 Indicator that the structure model may be wrong or deficient
1 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
1 ALERT type 5 Informative message, check
For both compounds, data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2008). Software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015) and PLATON (Spek, 2009) for (I); SHELXL2014 (Sheldrick, 2008) and PLATON (Spek, 2009) for (II).
(I) (
E)-4-[1-(2-Carbamothioylhydrazinylidene)ethyl]phenyl acetate
top
Crystal data top
| C11H13N3O2S | Z = 4 |
| Mr = 251.30 | F(000) = 528 |
| Triclinic, P1 | Dx = 1.330 Mg m−3 |
| a = 7.8783 (2) Å | Mo Kα radiation, λ = 0.71073 Å |
| b = 8.9254 (3) Å | Cell parameters from 5128 reflections |
| c = 18.7372 (5) Å | θ = 1.1–26.4° |
| α = 77.243 (2)° | µ = 0.25 mm−1 |
| β = 82.423 (2)° | T = 293 K |
| γ = 78.856 (2)° | Block, yellow |
| V = 1255.30 (6) Å3 | 0.20 × 0.15 × 0.10 mm |
Data collection top
Bruker SMART APEXII area-detector
diffractometer | 4104 reflections with I > 2σ(I) |
| ω and φ scans | Rint = 0.023 |
Absorption correction: multi-scan
(SADABS; Bruker, 2008) | θmax = 26.4°, θmin = 1.1° |
| Tmin = 0.785, Tmax = 0.854 | h = −9→9 |
| 18970 measured reflections | k = −11→11 |
| 5128 independent reflections | l = −23→23 |
Refinement top
| Refinement on F2 | Primary atom site location: structure-invariant direct methods |
| Least-squares matrix: full | Secondary atom site location: difference Fourier map |
| R[F2 > 2σ(F2)] = 0.038 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.109 | H-atom parameters constrained |
| S = 1.03 | w = 1/[σ2(Fo2) + (0.0498P)2 + 0.3822P]
where P = (Fo2 + 2Fc2)/3 |
| 5128 reflections | (Δ/σ)max = 0.001 |
| 311 parameters | Δρmax = 0.25 e Å−3 |
| 0 restraints | Δρmin = −0.31 e Å−3 |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top| | x | y | z | Uiso*/Ueq | |
| C10B | 0.2271 (3) | 0.1728 (3) | 0.52308 (11) | 0.0616 (5) | |
| H10A | 0.1335 | 0.2449 | 0.5001 | 0.092* | |
| H10B | 0.2263 | 0.1858 | 0.5726 | 0.092* | |
| H10C | 0.2129 | 0.0681 | 0.5235 | 0.092* | |
| C1A | 0.0183 (3) | 0.8835 (3) | 1.22191 (11) | 0.0706 (6) | |
| H1A1 | 0.0436 | 0.9807 | 1.2279 | 0.106* | |
| H1A2 | 0.0630 | 0.8015 | 1.2607 | 0.106* | |
| H1A3 | −0.1051 | 0.8899 | 1.2236 | 0.106* | |
| C1B | 0.5549 (3) | 0.0841 (3) | 0.07427 (10) | 0.0632 (5) | |
| H1B1 | 0.4721 | 0.1283 | 0.0388 | 0.095* | |
| H1B2 | 0.5685 | −0.0275 | 0.0835 | 0.095* | |
| H1B3 | 0.6646 | 0.1158 | 0.0556 | 0.095* | |
| C2A | 0.1010 (3) | 0.8500 (2) | 1.15003 (10) | 0.0506 (4) | |
| C2B | 0.4920 (3) | 0.1395 (2) | 0.14379 (9) | 0.0515 (4) | |
| C3A | 0.0618 (2) | 0.7263 (2) | 1.05471 (9) | 0.0438 (4) | |
| C3B | 0.5256 (3) | 0.0862 (2) | 0.27010 (9) | 0.0501 (4) | |
| C4A | −0.0202 (2) | 0.7922 (2) | 0.99205 (10) | 0.0497 (4) | |
| H4A | −0.1086 | 0.8781 | 0.9916 | 0.060* | |
| C4B | 0.6282 (3) | 0.1679 (2) | 0.29458 (10) | 0.0564 (5) | |
| H4B | 0.7253 | 0.1982 | 0.2652 | 0.068* | |
| C5A | 0.0297 (2) | 0.7298 (2) | 0.92993 (9) | 0.0476 (4) | |
| H5A | −0.0266 | 0.7738 | 0.8877 | 0.057* | |
| C5B | 0.5867 (3) | 0.2050 (2) | 0.36322 (9) | 0.0533 (5) | |
| H5B | 0.6566 | 0.2603 | 0.3800 | 0.064* | |
| C6A | 0.1629 (2) | 0.60209 (19) | 0.92929 (8) | 0.0396 (4) | |
| C6B | 0.4412 (2) | 0.16043 (19) | 0.40777 (9) | 0.0438 (4) | |
| C7A | 0.2445 (2) | 0.5402 (2) | 0.99344 (9) | 0.0459 (4) | |
| H7A | 0.3351 | 0.4559 | 0.9942 | 0.055* | |
| C7B | 0.3427 (3) | 0.0750 (2) | 0.38147 (10) | 0.0548 (5) | |
| H7B | 0.2464 | 0.0423 | 0.4106 | 0.066* | |
| C8A | 0.1934 (2) | 0.6015 (2) | 1.05617 (9) | 0.0481 (4) | |
| H8A | 0.2482 | 0.5581 | 1.0988 | 0.058* | |
| C8B | 0.3850 (3) | 0.0372 (2) | 0.31264 (10) | 0.0588 (5) | |
| H8B | 0.3182 | −0.0207 | 0.2958 | 0.071* | |
| C9A | 0.2116 (2) | 0.5324 (2) | 0.86296 (8) | 0.0412 (4) | |
| C9B | 0.3961 (2) | 0.20310 (19) | 0.48111 (9) | 0.0427 (4) | |
| C10A | 0.3766 (3) | 0.4199 (3) | 0.85640 (11) | 0.0705 (6) | |
| H10D | 0.4646 | 0.4736 | 0.8273 | 0.106* | |
| H10E | 0.3581 | 0.3395 | 0.8332 | 0.106* | |
| H10F | 0.4132 | 0.3743 | 0.9045 | 0.106* | |
| C11A | 0.0194 (2) | 0.5408 (2) | 0.70414 (9) | 0.0428 (4) | |
| C11B | 0.6013 (2) | 0.3524 (2) | 0.59815 (9) | 0.0448 (4) | |
| N1A | 0.10302 (18) | 0.57512 (17) | 0.81405 (7) | 0.0423 (3) | |
| N1B | 0.50947 (19) | 0.26330 (17) | 0.50292 (7) | 0.0460 (3) | |
| N2A | 0.14402 (18) | 0.52010 (17) | 0.74940 (7) | 0.0444 (3) | |
| H2A | 0.2473 | 0.4736 | 0.7384 | 0.053* | |
| N2B | 0.47614 (19) | 0.30636 (18) | 0.57038 (7) | 0.0483 (4) | |
| H2B | 0.3756 | 0.3037 | 0.5945 | 0.058* | |
| N3A | −0.1399 (2) | 0.5972 (2) | 0.72772 (8) | 0.0602 (4) | |
| H3A1 | −0.1609 | 0.6193 | 0.7708 | 0.072* | |
| H3A2 | −0.2229 | 0.6120 | 0.7001 | 0.072* | |
| N3B | 0.7503 (2) | 0.3608 (2) | 0.55723 (9) | 0.0641 (5) | |
| H3B1 | 0.7642 | 0.3371 | 0.5145 | 0.077* | |
| H3B2 | 0.8335 | 0.3898 | 0.5733 | 0.077* | |
| O1A | 0.2381 (2) | 0.8767 (2) | 1.12093 (9) | 0.0800 (5) | |
| O1B | 0.3862 (2) | 0.2510 (2) | 0.15026 (8) | 0.0863 (5) | |
| O2A | −0.00302 (17) | 0.78178 (16) | 1.11913 (7) | 0.0555 (3) | |
| O2B | 0.57246 (19) | 0.04701 (15) | 0.20057 (7) | 0.0607 (4) | |
| S1A | 0.07063 (6) | 0.49355 (7) | 0.62043 (2) | 0.05713 (16) | |
| S1B | 0.56754 (6) | 0.39051 (7) | 0.68325 (2) | 0.05582 (15) | |
Atomic displacement parameters (Å2) top| | U11 | U22 | U33 | U12 | U13 | U23 |
| C10B | 0.0553 (12) | 0.0813 (14) | 0.0553 (11) | −0.0165 (11) | 0.0010 (9) | −0.0283 (10) |
| C1A | 0.0818 (15) | 0.0834 (15) | 0.0541 (11) | −0.0020 (12) | −0.0163 (11) | −0.0344 (11) |
| C1B | 0.0750 (14) | 0.0799 (14) | 0.0428 (10) | −0.0222 (11) | 0.0034 (9) | −0.0265 (9) |
| C2A | 0.0566 (12) | 0.0518 (10) | 0.0477 (10) | −0.0062 (9) | −0.0142 (9) | −0.0161 (8) |
| C2B | 0.0558 (11) | 0.0610 (11) | 0.0406 (9) | −0.0078 (10) | −0.0053 (8) | −0.0179 (8) |
| C3A | 0.0435 (9) | 0.0564 (10) | 0.0378 (8) | −0.0175 (8) | 0.0009 (7) | −0.0177 (7) |
| C3B | 0.0664 (12) | 0.0445 (9) | 0.0384 (9) | 0.0034 (9) | −0.0108 (8) | −0.0140 (7) |
| C4A | 0.0490 (10) | 0.0543 (10) | 0.0488 (10) | −0.0039 (8) | −0.0074 (8) | −0.0192 (8) |
| C4B | 0.0699 (13) | 0.0590 (11) | 0.0427 (9) | −0.0163 (10) | 0.0035 (9) | −0.0158 (8) |
| C5A | 0.0514 (10) | 0.0539 (10) | 0.0396 (9) | −0.0061 (8) | −0.0110 (7) | −0.0126 (7) |
| C5B | 0.0665 (12) | 0.0565 (10) | 0.0428 (9) | −0.0181 (9) | −0.0010 (8) | −0.0181 (8) |
| C6A | 0.0379 (9) | 0.0493 (9) | 0.0352 (8) | −0.0144 (7) | −0.0021 (6) | −0.0106 (7) |
| C6B | 0.0530 (10) | 0.0417 (9) | 0.0364 (8) | −0.0031 (8) | −0.0094 (7) | −0.0086 (7) |
| C7A | 0.0440 (10) | 0.0544 (10) | 0.0394 (8) | −0.0043 (8) | −0.0064 (7) | −0.0118 (7) |
| C7B | 0.0580 (12) | 0.0644 (11) | 0.0464 (10) | −0.0153 (9) | −0.0054 (8) | −0.0157 (8) |
| C8A | 0.0500 (10) | 0.0623 (11) | 0.0340 (8) | −0.0116 (9) | −0.0081 (7) | −0.0095 (7) |
| C8B | 0.0694 (13) | 0.0628 (12) | 0.0530 (11) | −0.0124 (10) | −0.0154 (10) | −0.0235 (9) |
| C9A | 0.0368 (9) | 0.0536 (10) | 0.0352 (8) | −0.0112 (7) | −0.0013 (7) | −0.0113 (7) |
| C9B | 0.0452 (9) | 0.0456 (9) | 0.0365 (8) | −0.0022 (7) | −0.0078 (7) | −0.0093 (7) |
| C10A | 0.0578 (13) | 0.1042 (17) | 0.0488 (11) | 0.0159 (12) | −0.0143 (9) | −0.0341 (11) |
| C11A | 0.0387 (9) | 0.0554 (10) | 0.0362 (8) | −0.0082 (8) | −0.0039 (7) | −0.0130 (7) |
| C11B | 0.0403 (9) | 0.0559 (10) | 0.0388 (8) | −0.0021 (8) | −0.0052 (7) | −0.0153 (7) |
| N1A | 0.0410 (8) | 0.0560 (8) | 0.0335 (7) | −0.0104 (6) | −0.0013 (6) | −0.0158 (6) |
| N1B | 0.0477 (8) | 0.0579 (9) | 0.0338 (7) | −0.0041 (7) | −0.0047 (6) | −0.0156 (6) |
| N2A | 0.0355 (7) | 0.0657 (9) | 0.0349 (7) | −0.0049 (7) | −0.0024 (6) | −0.0202 (6) |
| N2B | 0.0397 (8) | 0.0720 (10) | 0.0371 (7) | −0.0072 (7) | −0.0011 (6) | −0.0228 (7) |
| N3A | 0.0410 (9) | 0.0971 (13) | 0.0450 (8) | 0.0060 (8) | −0.0084 (7) | −0.0322 (8) |
| N3B | 0.0451 (9) | 0.1090 (14) | 0.0489 (9) | −0.0192 (9) | 0.0046 (7) | −0.0384 (9) |
| O1A | 0.0727 (11) | 0.1024 (12) | 0.0834 (11) | −0.0401 (10) | 0.0012 (8) | −0.0408 (9) |
| O1B | 0.1032 (13) | 0.0907 (11) | 0.0507 (8) | 0.0349 (10) | −0.0177 (8) | −0.0223 (8) |
| O2A | 0.0525 (8) | 0.0791 (9) | 0.0448 (7) | −0.0190 (7) | 0.0029 (6) | −0.0311 (6) |
| O2B | 0.0776 (9) | 0.0599 (8) | 0.0442 (7) | 0.0098 (7) | −0.0114 (6) | −0.0246 (6) |
| S1A | 0.0422 (3) | 0.0971 (4) | 0.0381 (2) | −0.0090 (2) | −0.00201 (18) | −0.0298 (2) |
| S1B | 0.0444 (3) | 0.0874 (4) | 0.0418 (2) | −0.0056 (2) | −0.00359 (19) | −0.0310 (2) |
Geometric parameters (Å, º) top
| C10B—C9B | 1.494 (3) | C6A—C7A | 1.392 (2) |
| C10B—H10A | 0.9600 | C6A—C9A | 1.484 (2) |
| C10B—H10B | 0.9600 | C6B—C7B | 1.387 (2) |
| C10B—H10C | 0.9600 | C6B—C9B | 1.487 (2) |
| C1A—C2A | 1.483 (3) | C7A—C8A | 1.385 (2) |
| C1A—H1A1 | 0.9600 | C7A—H7A | 0.9300 |
| C1A—H1A2 | 0.9600 | C7B—C8B | 1.387 (2) |
| C1A—H1A3 | 0.9600 | C7B—H7B | 0.9300 |
| C1B—C2B | 1.485 (2) | C8A—H8A | 0.9300 |
| C1B—H1B1 | 0.9600 | C8B—H8B | 0.9300 |
| C1B—H1B2 | 0.9600 | C9A—N1A | 1.282 (2) |
| C1B—H1B3 | 0.9600 | C9A—C10A | 1.490 (3) |
| C2A—O1A | 1.186 (2) | C9B—N1B | 1.278 (2) |
| C2A—O2A | 1.361 (2) | C10A—H10D | 0.9600 |
| C2B—O1B | 1.186 (2) | C10A—H10E | 0.9600 |
| C2B—O2B | 1.343 (2) | C10A—H10F | 0.9600 |
| C3A—C8A | 1.366 (3) | C11A—N3A | 1.315 (2) |
| C3A—C4A | 1.375 (2) | C11A—N2A | 1.341 (2) |
| C3A—O2A | 1.4023 (19) | C11A—S1A | 1.6915 (16) |
| C3B—C8B | 1.361 (3) | C11B—N3B | 1.320 (2) |
| C3B—C4B | 1.367 (3) | C11B—N2B | 1.341 (2) |
| C3B—O2B | 1.4074 (19) | C11B—S1B | 1.6799 (16) |
| C4A—C5A | 1.379 (2) | N1A—N2A | 1.3825 (17) |
| C4A—H4A | 0.9300 | N1B—N2B | 1.3792 (18) |
| C4B—C5B | 1.381 (2) | N2A—H2A | 0.8600 |
| C4B—H4B | 0.9300 | N2B—H2B | 0.8600 |
| C5A—C6A | 1.394 (2) | N3A—H3A1 | 0.8600 |
| C5A—H5A | 0.9300 | N3A—H3A2 | 0.8600 |
| C5B—C6B | 1.395 (3) | N3B—H3B1 | 0.8600 |
| C5B—H5B | 0.9300 | N3B—H3B2 | 0.8600 |
| | | |
| C9B—C10B—H10A | 109.5 | C5B—C6B—C9B | 120.40 (15) |
| C9B—C10B—H10B | 109.5 | C8A—C7A—C6A | 121.27 (17) |
| H10A—C10B—H10B | 109.5 | C8A—C7A—H7A | 119.4 |
| C9B—C10B—H10C | 109.5 | C6A—C7A—H7A | 119.4 |
| H10A—C10B—H10C | 109.5 | C8B—C7B—C6B | 121.33 (18) |
| H10B—C10B—H10C | 109.5 | C8B—C7B—H7B | 119.3 |
| C2A—C1A—H1A1 | 109.5 | C6B—C7B—H7B | 119.3 |
| C2A—C1A—H1A2 | 109.5 | C3A—C8A—C7A | 119.29 (16) |
| H1A1—C1A—H1A2 | 109.5 | C3A—C8A—H8A | 120.4 |
| C2A—C1A—H1A3 | 109.5 | C7A—C8A—H8A | 120.4 |
| H1A1—C1A—H1A3 | 109.5 | C3B—C8B—C7B | 119.06 (17) |
| H1A2—C1A—H1A3 | 109.5 | C3B—C8B—H8B | 120.5 |
| C2B—C1B—H1B1 | 109.5 | C7B—C8B—H8B | 120.5 |
| C2B—C1B—H1B2 | 109.5 | N1A—C9A—C6A | 115.51 (15) |
| H1B1—C1B—H1B2 | 109.5 | N1A—C9A—C10A | 124.10 (15) |
| C2B—C1B—H1B3 | 109.5 | C6A—C9A—C10A | 120.39 (14) |
| H1B1—C1B—H1B3 | 109.5 | N1B—C9B—C6B | 115.48 (15) |
| H1B2—C1B—H1B3 | 109.5 | N1B—C9B—C10B | 125.51 (15) |
| O1A—C2A—O2A | 122.19 (17) | C6B—C9B—C10B | 119.01 (15) |
| O1A—C2A—C1A | 127.08 (18) | C9A—C10A—H10D | 109.5 |
| O2A—C2A—C1A | 110.72 (17) | C9A—C10A—H10E | 109.5 |
| O1B—C2B—O2B | 122.74 (16) | H10D—C10A—H10E | 109.5 |
| O1B—C2B—C1B | 126.04 (18) | C9A—C10A—H10F | 109.5 |
| O2B—C2B—C1B | 111.22 (17) | H10D—C10A—H10F | 109.5 |
| C8A—C3A—C4A | 121.15 (15) | H10E—C10A—H10F | 109.5 |
| C8A—C3A—O2A | 120.42 (15) | N3A—C11A—N2A | 117.60 (14) |
| C4A—C3A—O2A | 118.20 (16) | N3A—C11A—S1A | 122.72 (13) |
| C8B—C3B—C4B | 121.45 (16) | N2A—C11A—S1A | 119.68 (12) |
| C8B—C3B—O2B | 119.99 (17) | N3B—C11B—N2B | 117.47 (15) |
| C4B—C3B—O2B | 118.50 (17) | N3B—C11B—S1B | 122.55 (13) |
| C3A—C4A—C5A | 119.40 (17) | N2B—C11B—S1B | 119.94 (13) |
| C3A—C4A—H4A | 120.3 | C9A—N1A—N2A | 118.53 (14) |
| C5A—C4A—H4A | 120.3 | C9B—N1B—N2B | 118.72 (14) |
| C3B—C4B—C5B | 119.52 (18) | C11A—N2A—N1A | 118.60 (13) |
| C3B—C4B—H4B | 120.2 | C11A—N2A—H2A | 120.7 |
| C5B—C4B—H4B | 120.2 | N1A—N2A—H2A | 120.7 |
| C4A—C5A—C6A | 121.19 (16) | C11B—N2B—N1B | 119.63 (14) |
| C4A—C5A—H5A | 119.4 | C11B—N2B—H2B | 120.2 |
| C6A—C5A—H5A | 119.4 | N1B—N2B—H2B | 120.2 |
| C4B—C5B—C6B | 120.83 (17) | C11A—N3A—H3A1 | 120.0 |
| C4B—C5B—H5B | 119.6 | C11A—N3A—H3A2 | 120.0 |
| C6B—C5B—H5B | 119.6 | H3A1—N3A—H3A2 | 120.0 |
| C7A—C6A—C5A | 117.68 (15) | C11B—N3B—H3B1 | 120.0 |
| C7A—C6A—C9A | 121.51 (15) | C11B—N3B—H3B2 | 120.0 |
| C5A—C6A—C9A | 120.79 (14) | H3B1—N3B—H3B2 | 120.0 |
| C7B—C6B—C5B | 117.77 (16) | C2A—O2A—C3A | 118.74 (14) |
| C7B—C6B—C9B | 121.82 (16) | C2B—O2B—C3B | 117.30 (14) |
| | | |
| C8A—C3A—C4A—C5A | 0.9 (3) | C5A—C6A—C9A—C10A | 166.64 (18) |
| O2A—C3A—C4A—C5A | −173.63 (15) | C7B—C6B—C9B—N1B | 170.96 (17) |
| C8B—C3B—C4B—C5B | −1.6 (3) | C5B—C6B—C9B—N1B | −8.5 (2) |
| O2B—C3B—C4B—C5B | −178.73 (17) | C7B—C6B—C9B—C10B | −8.7 (3) |
| C3A—C4A—C5A—C6A | −0.6 (3) | C5B—C6B—C9B—C10B | 171.80 (17) |
| C3B—C4B—C5B—C6B | −0.1 (3) | C6A—C9A—N1A—N2A | 177.13 (13) |
| C4A—C5A—C6A—C7A | −0.3 (3) | C10A—C9A—N1A—N2A | −3.3 (3) |
| C4A—C5A—C6A—C9A | 177.89 (16) | C6B—C9B—N1B—N2B | 179.76 (14) |
| C4B—C5B—C6B—C7B | 1.4 (3) | C10B—C9B—N1B—N2B | −0.6 (3) |
| C4B—C5B—C6B—C9B | −179.04 (17) | N3A—C11A—N2A—N1A | −7.3 (2) |
| C5A—C6A—C7A—C8A | 1.0 (2) | S1A—C11A—N2A—N1A | 173.06 (12) |
| C9A—C6A—C7A—C8A | −177.17 (15) | C9A—N1A—N2A—C11A | 168.09 (16) |
| C5B—C6B—C7B—C8B | −1.2 (3) | N3B—C11B—N2B—N1B | 3.0 (3) |
| C9B—C6B—C7B—C8B | 179.30 (17) | S1B—C11B—N2B—N1B | −174.85 (12) |
| C4A—C3A—C8A—C7A | −0.2 (3) | C9B—N1B—N2B—C11B | 172.12 (16) |
| O2A—C3A—C8A—C7A | 174.20 (15) | O1A—C2A—O2A—C3A | 7.0 (3) |
| C6A—C7A—C8A—C3A | −0.8 (3) | C1A—C2A—O2A—C3A | −173.17 (16) |
| C4B—C3B—C8B—C7B | 1.8 (3) | C8A—C3A—O2A—C2A | 67.9 (2) |
| O2B—C3B—C8B—C7B | 178.94 (17) | C4A—C3A—O2A—C2A | −117.52 (19) |
| C6B—C7B—C8B—C3B | −0.4 (3) | O1B—C2B—O2B—C3B | 0.6 (3) |
| C7A—C6A—C9A—N1A | 164.41 (16) | C1B—C2B—O2B—C3B | 179.85 (16) |
| C5A—C6A—C9A—N1A | −13.8 (2) | C8B—C3B—O2B—C2B | 84.9 (2) |
| C7A—C6A—C9A—C10A | −15.2 (3) | C4B—C3B—O2B—C2B | −97.9 (2) |
Hydrogen-bond geometry (Å, º) top| Cg1 and Cg2 are the centroids of the C3A–C8A and
C3B–C8B rings,
respectively. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| N3A—H3A1···N1A | 0.86 | 2.26 | 2.617 (2) | 105 |
| N3B—H3B1···N1B | 0.86 | 2.28 | 2.633 (2) | 105 |
| N2A—H2A···S1B | 0.86 | 2.63 | 3.4724 (15) | 167 |
| N2B—H2B···S1A | 0.86 | 2.71 | 3.4228 (16) | 141 |
| N3A—H3A1···O1Bi | 0.86 | 2.44 | 3.164 (2) | 142 |
| N3B—H3B2···S1Aii | 0.86 | 2.57 | 3.4262 (17) | 176 |
| N3A—H3A2···Cg2iii | 0.86 | 2.62 | 3.4763 (19) | 130 |
| C1B—H1B3···Cg1iv | 0.96 | 2.73 | 3.691 (3) | 154 |
| Symmetry codes: (i) −x, −y+1, −z+1; (ii) x+1, y, z; (iii) −x, −y+1, −z; (iv) −x+1, −y+1, −z. |
(II) (
E)-4-[1-(2-Carbamothioylhydrazinylidene)ethyl]phenyl benzoate
top
Crystal data top
| C16H15N3O2S | Z = 2 |
| Mr = 313.37 | F(000) = 328 |
| Triclinic, P1 | Dx = 1.367 Mg m−3 |
| a = 7.8145 (4) Å | Mo Kα radiation, λ = 0.71073 Å |
| b = 9.7538 (5) Å | Cell parameters from 3154 reflections |
| c = 10.9050 (7) Å | θ = 2.0–26.5° |
| α = 78.855 (4)° | µ = 0.22 mm−1 |
| β = 69.031 (2)° | T = 293 K |
| γ = 84.200 (3)° | Block, pale-yellow |
| V = 761.05 (8) Å3 | 0.25 × 0.18 × 0.14 mm |
Data collection top
Bruker SMART APEXII area-detector
diffractometer | 2857 reflections with I > 2σ(I) |
| ω and φ scans | Rint = 0.027 |
Absorption correction: multi-scan
(SADABS; Bruker, 2008) | θmax = 26.5°, θmin = 2.0° |
| Tmin = 0.745, Tmax = 0.865 | h = −8→9 |
| 11596 measured reflections | k = −12→12 |
| 3154 independent reflections | l = −13→13 |
Refinement top
| Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
| Least-squares matrix: full | H-atom parameters constrained |
| R[F2 > 2σ(F2)] = 0.034 | w = 1/[σ2(Fo2) + (0.0512P)2 + 0.1914P]
where P = (Fo2 + 2Fc2)/3 |
| wR(F2) = 0.099 | (Δ/σ)max = 0.001 |
| S = 1.05 | Δρmax = 0.26 e Å−3 |
| 3154 reflections | Δρmin = −0.29 e Å−3 |
| 201 parameters | Extinction correction: SHELXL2014 (Sheldrick, 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
| 0 restraints | Extinction coefficient: 0.080 (6) |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top| | x | y | z | Uiso*/Ueq | |
| C1 | −0.0574 (2) | 0.60395 (15) | 0.12357 (14) | 0.0461 (3) | |
| H1 | 0.0581 | 0.6165 | 0.1252 | 0.055* | |
| C2 | −0.1286 (2) | 0.69706 (17) | 0.03984 (16) | 0.0562 (4) | |
| H2 | −0.0616 | 0.7736 | −0.0138 | 0.067* | |
| C3 | −0.2978 (3) | 0.67730 (18) | 0.03519 (16) | 0.0596 (4) | |
| H3 | −0.3439 | 0.7398 | −0.0223 | 0.072* | |
| C4 | −0.3993 (2) | 0.56519 (19) | 0.11541 (17) | 0.0579 (4) | |
| H4 | −0.5134 | 0.5519 | 0.1117 | 0.069* | |
| C5 | −0.3315 (2) | 0.47264 (16) | 0.20141 (15) | 0.0483 (3) | |
| H5 | −0.4005 | 0.3977 | 0.2567 | 0.058* | |
| C6 | −0.15975 (18) | 0.49176 (14) | 0.20510 (12) | 0.0384 (3) | |
| C7 | −0.09783 (18) | 0.39381 (14) | 0.30353 (12) | 0.0392 (3) | |
| C8 | 0.15463 (18) | 0.31751 (15) | 0.37198 (13) | 0.0400 (3) | |
| C9 | 0.15816 (19) | 0.17391 (15) | 0.39018 (14) | 0.0442 (3) | |
| H9 | 0.1159 | 0.1286 | 0.3395 | 0.053* | |
| C10 | 0.22566 (19) | 0.09777 (14) | 0.48531 (14) | 0.0412 (3) | |
| H10 | 0.2247 | 0.0006 | 0.5004 | 0.049* | |
| C11 | 0.29489 (16) | 0.16457 (13) | 0.55862 (12) | 0.0346 (3) | |
| C12 | 0.29666 (19) | 0.31025 (14) | 0.53336 (14) | 0.0406 (3) | |
| H12 | 0.3466 | 0.3565 | 0.5790 | 0.049* | |
| C13 | 0.22498 (19) | 0.38662 (14) | 0.44118 (14) | 0.0433 (3) | |
| H13 | 0.2243 | 0.4838 | 0.4260 | 0.052* | |
| C14 | 0.36348 (17) | 0.08555 (13) | 0.66391 (12) | 0.0353 (3) | |
| C15 | 0.2849 (2) | −0.05203 (16) | 0.73732 (16) | 0.0549 (4) | |
| H15A | 0.3642 | −0.1019 | 0.7820 | 0.082* | |
| H15B | 0.2737 | −0.1056 | 0.6755 | 0.082* | |
| H15C | 0.1661 | −0.0373 | 0.8018 | 0.082* | |
| C16 | 0.70223 (17) | 0.13075 (13) | 0.78932 (12) | 0.0358 (3) | |
| N1 | 0.48733 (14) | 0.14652 (11) | 0.68311 (10) | 0.0361 (2) | |
| N2 | 0.54777 (15) | 0.08471 (11) | 0.78611 (11) | 0.0374 (2) | |
| H2A | 0.4883 | 0.0188 | 0.8464 | 0.045* | |
| N3 | 0.79854 (16) | 0.21798 (13) | 0.68277 (11) | 0.0467 (3) | |
| H3A | 0.7611 | 0.2423 | 0.6162 | 0.056* | |
| H3B | 0.8984 | 0.2502 | 0.6803 | 0.056* | |
| O1 | −0.19599 (15) | 0.31803 (12) | 0.39711 (10) | 0.0550 (3) | |
| O2 | 0.08423 (13) | 0.40017 (11) | 0.27880 (9) | 0.0477 (3) | |
| S1 | 0.77088 (5) | 0.07598 (4) | 0.92056 (4) | 0.05405 (15) | |
Atomic displacement parameters (Å2) top| | U11 | U22 | U33 | U12 | U13 | U23 |
| C1 | 0.0487 (8) | 0.0491 (8) | 0.0399 (7) | −0.0026 (6) | −0.0165 (6) | −0.0032 (6) |
| C2 | 0.0671 (10) | 0.0487 (8) | 0.0458 (8) | 0.0029 (7) | −0.0183 (7) | 0.0033 (6) |
| C3 | 0.0728 (11) | 0.0613 (10) | 0.0465 (8) | 0.0207 (8) | −0.0300 (8) | −0.0070 (7) |
| C4 | 0.0528 (9) | 0.0721 (10) | 0.0583 (9) | 0.0112 (8) | −0.0323 (8) | −0.0149 (8) |
| C5 | 0.0451 (8) | 0.0555 (8) | 0.0467 (8) | −0.0013 (6) | −0.0206 (6) | −0.0055 (6) |
| C6 | 0.0423 (7) | 0.0432 (7) | 0.0315 (6) | 0.0014 (5) | −0.0157 (5) | −0.0067 (5) |
| C7 | 0.0409 (7) | 0.0454 (7) | 0.0333 (6) | −0.0030 (5) | −0.0159 (5) | −0.0048 (5) |
| C8 | 0.0341 (6) | 0.0523 (7) | 0.0320 (6) | −0.0008 (5) | −0.0134 (5) | 0.0004 (5) |
| C9 | 0.0457 (7) | 0.0526 (8) | 0.0419 (7) | 0.0009 (6) | −0.0224 (6) | −0.0131 (6) |
| C10 | 0.0426 (7) | 0.0409 (7) | 0.0447 (7) | 0.0023 (5) | −0.0196 (6) | −0.0112 (5) |
| C11 | 0.0308 (6) | 0.0398 (6) | 0.0328 (6) | 0.0008 (5) | −0.0115 (5) | −0.0055 (5) |
| C12 | 0.0425 (7) | 0.0419 (7) | 0.0429 (7) | −0.0020 (5) | −0.0211 (6) | −0.0073 (5) |
| C13 | 0.0451 (7) | 0.0394 (7) | 0.0473 (7) | −0.0026 (5) | −0.0214 (6) | −0.0006 (5) |
| C14 | 0.0332 (6) | 0.0384 (6) | 0.0345 (6) | 0.0000 (5) | −0.0128 (5) | −0.0054 (5) |
| C15 | 0.0616 (10) | 0.0520 (8) | 0.0568 (9) | −0.0181 (7) | −0.0328 (8) | 0.0094 (7) |
| C16 | 0.0333 (6) | 0.0364 (6) | 0.0365 (6) | −0.0022 (5) | −0.0130 (5) | −0.0010 (5) |
| N1 | 0.0360 (5) | 0.0396 (5) | 0.0339 (5) | −0.0005 (4) | −0.0162 (4) | −0.0013 (4) |
| N2 | 0.0365 (6) | 0.0404 (6) | 0.0354 (5) | −0.0073 (4) | −0.0166 (4) | 0.0047 (4) |
| N3 | 0.0427 (6) | 0.0574 (7) | 0.0394 (6) | −0.0168 (5) | −0.0187 (5) | 0.0098 (5) |
| O1 | 0.0480 (6) | 0.0675 (7) | 0.0456 (6) | −0.0137 (5) | −0.0208 (5) | 0.0146 (5) |
| O2 | 0.0404 (5) | 0.0622 (6) | 0.0387 (5) | −0.0055 (4) | −0.0193 (4) | 0.0083 (4) |
| S1 | 0.0454 (2) | 0.0720 (3) | 0.0464 (2) | −0.01842 (18) | −0.02749 (17) | 0.01713 (18) |
Geometric parameters (Å, º) top
| C1—C2 | 1.381 (2) | C10—C11 | 1.3923 (18) |
| C1—C6 | 1.3853 (19) | C10—H10 | 0.9300 |
| C1—H1 | 0.9300 | C11—C12 | 1.3947 (18) |
| C2—C3 | 1.375 (3) | C11—C14 | 1.4881 (17) |
| C2—H2 | 0.9300 | C12—C13 | 1.3815 (18) |
| C3—C4 | 1.378 (3) | C12—H12 | 0.9300 |
| C3—H3 | 0.9300 | C13—H13 | 0.9300 |
| C4—C5 | 1.381 (2) | C14—N1 | 1.2820 (16) |
| C4—H4 | 0.9300 | C14—C15 | 1.4894 (18) |
| C5—C6 | 1.389 (2) | C15—H15A | 0.9600 |
| C5—H5 | 0.9300 | C15—H15B | 0.9600 |
| C6—C7 | 1.4767 (17) | C15—H15C | 0.9600 |
| C7—O1 | 1.1995 (16) | C16—N3 | 1.3273 (16) |
| C7—O2 | 1.3555 (16) | C16—N2 | 1.3437 (16) |
| C8—C9 | 1.375 (2) | C16—S1 | 1.6785 (13) |
| C8—C13 | 1.376 (2) | N1—N2 | 1.3816 (14) |
| C8—O2 | 1.4067 (15) | N2—H2A | 0.8600 |
| C9—C10 | 1.3858 (19) | N3—H3A | 0.8600 |
| C9—H9 | 0.9300 | N3—H3B | 0.8600 |
| | | |
| C2—C1—C6 | 119.40 (14) | C10—C11—C12 | 118.52 (12) |
| C2—C1—H1 | 120.3 | C10—C11—C14 | 122.07 (11) |
| C6—C1—H1 | 120.3 | C12—C11—C14 | 119.40 (11) |
| C3—C2—C1 | 120.47 (15) | C13—C12—C11 | 120.66 (12) |
| C3—C2—H2 | 119.8 | C13—C12—H12 | 119.7 |
| C1—C2—H2 | 119.8 | C11—C12—H12 | 119.7 |
| C2—C3—C4 | 120.27 (14) | C8—C13—C12 | 119.37 (13) |
| C2—C3—H3 | 119.9 | C8—C13—H13 | 120.3 |
| C4—C3—H3 | 119.9 | C12—C13—H13 | 120.3 |
| C3—C4—C5 | 119.92 (16) | N1—C14—C11 | 114.67 (11) |
| C3—C4—H4 | 120.0 | N1—C14—C15 | 126.07 (12) |
| C5—C4—H4 | 120.0 | C11—C14—C15 | 119.26 (11) |
| C4—C5—C6 | 119.80 (14) | C14—C15—H15A | 109.5 |
| C4—C5—H5 | 120.1 | C14—C15—H15B | 109.5 |
| C6—C5—H5 | 120.1 | H15A—C15—H15B | 109.5 |
| C1—C6—C5 | 120.12 (13) | C14—C15—H15C | 109.5 |
| C1—C6—C7 | 122.27 (12) | H15A—C15—H15C | 109.5 |
| C5—C6—C7 | 117.51 (12) | H15B—C15—H15C | 109.5 |
| O1—C7—O2 | 122.72 (12) | N3—C16—N2 | 116.66 (11) |
| O1—C7—C6 | 124.71 (12) | N3—C16—S1 | 122.30 (10) |
| O2—C7—C6 | 112.56 (11) | N2—C16—S1 | 121.02 (9) |
| C9—C8—C13 | 121.44 (12) | C14—N1—N2 | 118.03 (10) |
| C9—C8—O2 | 121.45 (12) | C16—N2—N1 | 117.98 (10) |
| C13—C8—O2 | 117.08 (12) | C16—N2—H2A | 121.0 |
| C8—C9—C10 | 118.95 (12) | N1—N2—H2A | 121.0 |
| C8—C9—H9 | 120.5 | C16—N3—H3A | 120.0 |
| C10—C9—H9 | 120.5 | C16—N3—H3B | 120.0 |
| C9—C10—C11 | 120.96 (12) | H3A—N3—H3B | 120.0 |
| C9—C10—H10 | 119.5 | C7—O2—C8 | 116.96 (10) |
| C11—C10—H10 | 119.5 | | |
| | | |
| C6—C1—C2—C3 | −1.3 (2) | C14—C11—C12—C13 | −176.57 (12) |
| C1—C2—C3—C4 | 0.8 (3) | C9—C8—C13—C12 | −1.6 (2) |
| C2—C3—C4—C5 | 0.4 (3) | O2—C8—C13—C12 | −179.67 (12) |
| C3—C4—C5—C6 | −1.0 (2) | C11—C12—C13—C8 | −1.3 (2) |
| C2—C1—C6—C5 | 0.7 (2) | C10—C11—C14—N1 | 152.10 (12) |
| C2—C1—C6—C7 | −175.72 (13) | C12—C11—C14—N1 | −28.98 (17) |
| C4—C5—C6—C1 | 0.5 (2) | C10—C11—C14—C15 | −28.60 (19) |
| C4—C5—C6—C7 | 177.06 (13) | C12—C11—C14—C15 | 150.32 (14) |
| C1—C6—C7—O1 | 160.66 (14) | C11—C14—N1—N2 | 175.16 (10) |
| C5—C6—C7—O1 | −15.8 (2) | C15—C14—N1—N2 | −4.1 (2) |
| C1—C6—C7—O2 | −18.01 (18) | N3—C16—N2—N1 | −9.43 (18) |
| C5—C6—C7—O2 | 165.53 (12) | S1—C16—N2—N1 | 172.24 (9) |
| C13—C8—C9—C10 | 3.3 (2) | C14—N1—N2—C16 | 166.17 (12) |
| O2—C8—C9—C10 | −178.70 (12) | O1—C7—O2—C8 | −2.8 (2) |
| C8—C9—C10—C11 | −2.2 (2) | C6—C7—O2—C8 | 175.91 (11) |
| C9—C10—C11—C12 | −0.6 (2) | C9—C8—O2—C7 | 66.31 (17) |
| C9—C10—C11—C14 | 178.29 (12) | C13—C8—O2—C7 | −115.64 (14) |
| C10—C11—C12—C13 | 2.4 (2) | | |
Hydrogen-bond geometry (Å, º) top| Cg2 is the centroid of the C8–C13 ring. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| N3—H3A···N1 | 0.86 | 2.24 | 2.5953 (18) | 105 |
| N2—H2A···S1i | 0.86 | 2.68 | 3.4697 (12) | 153 |
| N3—H3A···O1ii | 0.86 | 2.27 | 3.0653 (15) | 153 |
| C15—H15B···O1iii | 0.96 | 2.55 | 3.454 (2) | 156 |
| N3—H3B···Cg2ii | 0.86 | 2.47 | 3.3385 (15) | 122 |
| Symmetry codes: (i) −x+1, −y, −z+2; (ii) x+1, y, z; (iii) −x, −y, −z+1. |
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(8) ring motifs.
